CA1078843A - Process for the preparation of new thienopyridine derivatives - Google Patents
Process for the preparation of new thienopyridine derivativesInfo
- Publication number
- CA1078843A CA1078843A CA256,470A CA256470A CA1078843A CA 1078843 A CA1078843 A CA 1078843A CA 256470 A CA256470 A CA 256470A CA 1078843 A CA1078843 A CA 1078843A
- Authority
- CA
- Canada
- Prior art keywords
- radical
- organic acid
- acid addition
- quaternary ammonium
- group selected
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- 238000002360 preparation method Methods 0.000 title claims abstract description 11
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 26
- -1 cyano, hydroxymethyl Chemical group 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
- 239000001257 hydrogen Substances 0.000 claims abstract description 20
- 150000007522 mineralic acids Chemical class 0.000 claims abstract description 20
- 150000007524 organic acids Chemical class 0.000 claims abstract description 20
- 101100097467 Arabidopsis thaliana SYD gene Proteins 0.000 claims abstract description 19
- 101100495925 Schizosaccharomyces pombe (strain 972 / ATCC 24843) chr3 gene Proteins 0.000 claims abstract description 19
- 125000005843 halogen group Chemical group 0.000 claims abstract description 18
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims abstract description 13
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 150000002367 halogens Chemical class 0.000 claims abstract description 11
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 9
- 239000000463 material Substances 0.000 claims abstract description 9
- 125000005504 styryl group Chemical group 0.000 claims abstract description 8
- WJFYLCXWEXZNHU-UHFFFAOYSA-N 2,3,3a,4-tetrahydrothieno[3,2-b]pyridine Chemical compound N1C=CC=C2SCCC21 WJFYLCXWEXZNHU-UHFFFAOYSA-N 0.000 claims abstract description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 150000002148 esters Chemical group 0.000 claims description 5
- 230000003301 hydrolyzing effect Effects 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- QKASDIPENBEWBU-UHFFFAOYSA-N methyl 2-(bromomethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CBr QKASDIPENBEWBU-UHFFFAOYSA-N 0.000 claims description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
- 238000006482 condensation reaction Methods 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 4
- 239000000126 substance Substances 0.000 claims 4
- CTPYPCDNYYPXAG-UHFFFAOYSA-N 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)benzonitrile Chemical compound N#CC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 CTPYPCDNYYPXAG-UHFFFAOYSA-N 0.000 claims 2
- MJCCFKPVHQYONK-UHFFFAOYSA-N methyl 2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1CN1CC(C=CS2)=C2CC1 MJCCFKPVHQYONK-UHFFFAOYSA-N 0.000 claims 2
- QGXNHCXKWFNKCG-UHFFFAOYSA-N 2-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=CC=C1C#N QGXNHCXKWFNKCG-UHFFFAOYSA-N 0.000 claims 1
- OGUWOLDNYOTRBO-UHFFFAOYSA-N 4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1NCCC2=C1C=CS2 OGUWOLDNYOTRBO-UHFFFAOYSA-N 0.000 claims 1
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 11
- 210000001772 blood platelet Anatomy 0.000 abstract description 11
- 230000003110 anti-inflammatory effect Effects 0.000 abstract description 7
- 229940124549 vasodilator Drugs 0.000 abstract description 7
- 239000003071 vasodilator agent Substances 0.000 abstract description 7
- 239000003112 inhibitor Substances 0.000 abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 6
- 125000003277 amino group Chemical group 0.000 abstract description 4
- 125000003118 aryl group Chemical group 0.000 abstract description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract description 3
- 125000004429 atom Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract description 2
- 150000003222 pyridines Chemical class 0.000 abstract description 2
- 125000001544 thienyl group Chemical group 0.000 abstract description 2
- 230000004931 aggregating effect Effects 0.000 abstract 1
- 125000004185 ester group Chemical group 0.000 abstract 1
- 229940125670 thienopyridine Drugs 0.000 abstract 1
- 239000002175 thienopyridine Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 206010030113 Oedema Diseases 0.000 description 6
- 238000011835 investigation Methods 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 239000003826 tablet Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 108010058846 Ovalbumin Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 230000002490 cerebral effect Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 150000002500 ions Chemical class 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 229940092253 ovalbumin Drugs 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 210000002966 serum Anatomy 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 241000790917 Dioxys <bee> Species 0.000 description 2
- 206010061218 Inflammation Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 230000004054 inflammatory process Effects 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000011976 maleic acid Substances 0.000 description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- QLSJOGIENLKPTF-WLHGVMLRSA-N (e)-but-2-enedioic acid;pyridine Chemical compound C1=CC=NC=C1.OC(=O)\C=C\C(O)=O QLSJOGIENLKPTF-WLHGVMLRSA-N 0.000 description 1
- FRTAFUJREBRRJD-BTJKTKAUSA-N (z)-but-2-enedioic acid;2-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-ylmethyl)benzonitrile Chemical compound OC(=O)\C=C/C(O)=O.N#CC1=CC=CC=C1CN1CC(C=CS2)=C2CC1 FRTAFUJREBRRJD-BTJKTKAUSA-N 0.000 description 1
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 206010002383 Angina Pectoris Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229940127218 antiplatelet drug Drugs 0.000 description 1
- 210000004204 blood vessel Anatomy 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 206010006451 bronchitis Diseases 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000002316 cosmetic surgery Methods 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- FHHZOYXKOICLGH-UHFFFAOYSA-N dichloromethane;ethanol Chemical compound CCO.ClCCl FHHZOYXKOICLGH-UHFFFAOYSA-N 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 239000006196 drop Substances 0.000 description 1
- 230000002526 effect on cardiovascular system Effects 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 208000014674 injury Diseases 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 210000003141 lower extremity Anatomy 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 230000008520 organization Effects 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000036513 peripheral conductance Effects 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- LEVJVKGPFAQPOI-UHFFFAOYSA-N phenylmethanone Chemical group O=[C]C1=CC=CC=C1 LEVJVKGPFAQPOI-UHFFFAOYSA-N 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- 239000000106 platelet aggregation inhibitor Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 1
- 229940100486 rice starch Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000009885 systemic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- 238000007817 turbidimetric assay Methods 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7524486A FR2345150A2 (fr) | 1975-08-06 | 1975-08-06 | Nouveaux derives de la thienopyridine, et leur application |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1078843A true CA1078843A (en) | 1980-06-03 |
Family
ID=9158816
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA256,470A Expired CA1078843A (en) | 1975-08-06 | 1976-07-07 | Process for the preparation of new thienopyridine derivatives |
Country Status (29)
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2336932A2 (fr) * | 1973-02-01 | 1977-07-29 | Centre Etd Ind Pharma | Derives pyridiniques, leur preparation et leurs applications |
| FR2395271A1 (fr) * | 1977-06-21 | 1979-01-19 | Parcor | Procede de preparation de thieno (2,3-c) et thieno (3,2-c) pyridines |
| GB2038625B (en) * | 1978-12-29 | 1983-01-12 | Parcor | Therapeutic composition having an antithrombotic and antiblood-platelet-aggregating activity |
| US4749692A (en) * | 1977-06-22 | 1988-06-07 | Sanofi, S.A. | Therapeutic compositions having anti-thrombotic and anti-blood-platelet-aggregating activity |
| US4464377A (en) * | 1977-06-22 | 1984-08-07 | BLANCHARD Jean | Anti-thrombotic therapeutic compositions |
| US4400384A (en) * | 1980-10-06 | 1983-08-23 | Sanofi, S.A. | 5-o-Cyanobenzyl-4,5,6,7-tetrahydrothieno [3,2-c] pyridine methanesulfonate and other novel salts thereof |
| US4321266A (en) * | 1980-10-06 | 1982-03-23 | Sanofi | 5-o-Cyanobenzyl-4,5,6,7-tetrahydrothieno [3,2-C] pyridine |
| FR2495156A1 (fr) * | 1980-11-28 | 1982-06-04 | Sanofi Sa | Derives de la thieno-pyridinone, leur procede de preparation et leur application therapeutique |
| FR2495157A1 (fr) | 1980-11-28 | 1982-06-04 | Sanofi Sa | Procede nouveau de preparation des tetrahydro-5, 6, 7, 7a 4h-thieno (3, 2-c) pyridinones-2 |
| FR2508442A1 (fr) * | 1981-06-30 | 1982-12-31 | Sanofi Sa | Procede de preparation d'ethylamines b-cyclo-substituees et produits ainsi obtenus |
| US4448779A (en) * | 1981-07-16 | 1984-05-15 | Sanofi | Use of MS salt in geriatric medicine |
| FR2612777A1 (fr) * | 1987-03-26 | 1988-09-30 | Inst Nat Sante Rech Med | Composition medicamenteuse pour le traitement et la prevention de maladies dues a une cytotoxicite a mediation cellulaire, renfermant au moins un derive de la pyridine comme principe actif |
| JPH01178056U (enrdf_load_stackoverflow) * | 1988-06-01 | 1989-12-20 | ||
| ATE407675T1 (de) | 2000-12-25 | 2008-09-15 | Daiichi Sankyo Co Ltd | Aspirin enthaltende medizinische zusammensetzungen |
| CN102241690B (zh) * | 2010-05-13 | 2015-08-12 | 天津药物研究院 | 一类含腈基的噻吩并吡啶酯类衍生物、其制备方法和用途 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215948B1 (enrdf_load_stackoverflow) * | 1973-02-01 | 1976-05-14 | Centre Etd Ind Pharma | |
| FR2278683A1 (fr) * | 1974-07-16 | 1976-02-13 | Parcor | Procede de preparation de la thieno(3,2-c)pyridine et de la thieno(2,3-c)pyridine |
-
1975
- 1975-08-06 FR FR7524486A patent/FR2345150A2/fr active Granted
-
1976
- 1976-05-25 CH CH656776A patent/CH612680A5/xx not_active IP Right Cessation
- 1976-05-31 BE BE167464A patent/BE842379R/xx not_active IP Right Cessation
- 1976-06-04 YU YU1378/76A patent/YU39967B/xx unknown
- 1976-06-30 NL NLAANVRAGE7607254,A patent/NL183825C/xx not_active IP Right Cessation
- 1976-07-07 CA CA256,470A patent/CA1078843A/en not_active Expired
- 1976-07-08 IE IE1509/76A patent/IE44122B1/en unknown
- 1976-07-09 US US05/703,837 patent/US4097482A/en not_active Expired - Lifetime
- 1976-07-12 ZA ZA764122A patent/ZA764122B/xx unknown
- 1976-07-20 ES ES449963A patent/ES449963A2/es not_active Expired
- 1976-07-30 DK DK344076A patent/DK149816C/da not_active IP Right Cessation
- 1976-08-02 FI FI762198A patent/FI60206C/fi not_active IP Right Cessation
- 1976-08-02 MX MX762119U patent/MX3744E/es unknown
- 1976-08-03 DE DE2634903A patent/DE2634903C2/de not_active Expired
- 1976-08-03 SE SE7608691A patent/SE421795B/xx not_active IP Right Cessation
- 1976-08-03 AU AU16525/76A patent/AU503800B2/en not_active Expired
- 1976-08-03 RO RO7687201A patent/RO70615A/ro unknown
- 1976-08-03 GB GB32335/76A patent/GB1561504A/en not_active Expired
- 1976-08-04 LU LU75534A patent/LU75534A1/xx unknown
- 1976-08-04 AT AT577576A patent/AT350570B/de not_active IP Right Cessation
- 1976-08-04 DD DD194210A patent/DD126296A6/xx unknown
- 1976-08-05 PH PH7618763A patent/PH12369A/en unknown
- 1976-08-05 NO NO762714A patent/NO143225C/no unknown
- 1976-08-05 HU HU76CE1102A patent/HU174548B/hu not_active IP Right Cessation
- 1976-08-05 SU SU762386212A patent/SU626701A3/ru active
- 1976-08-05 PL PL1976191647A patent/PL117046B1/pl not_active IP Right Cessation
- 1976-08-05 NZ NZ181687A patent/NZ181687A/xx unknown
- 1976-08-06 AR AR264267A patent/AR217629A1/es active
- 1976-08-06 JP JP51093890A patent/JPS5219696A/ja active Granted
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